ChemSpider 2D Image | Tobramycin | C18H37N5O9

Tobramycin

  • Molecular FormulaC18H37N5O9
  • Average mass467.514 Da
  • Monoisotopic mass467.259125 Da
  • ChemSpider ID33377
  • defined stereocentres - 14 of 14 defined stereocentres


More details:



Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2,6-diamino-2,3,6-trideoxy-a-D-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-a-D-glucopyranoside
(1S,2S,3R,4S,6R)-4,6-Diamino-3-[(2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-α-D-glucopyranoside [ACD/IUPAC Name]
(2S,3R,4S,5S,6R)-4-Amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran
(2S,3R,4S,5S,6R)-4-Amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol
(2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminométhyl)-5-hydroxytétrahydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxyméthyl)tétrahydro-2H-pyran-3,5-diol
251-322-5 [EINECS]
2990
32986-56-4 [RN]
3-Amino-3-désoxy-α-D-glucopyranoside de (1S,2S,3R,4S,6R)-4,6-diamino-3-[(2,6-diamino-2,3,6-tridésoxy-α-D-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyle [French] [ACD/IUPAC Name]
4-[2,6-Diamino-2,3,6-trideoxy-a-D-glycopyranosyl]-6-[3-amino-3-deoxy-a-D-glycopyranosyl]-2-deoxystreptamine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS005088 [DBID]
AIDS-005088 [DBID]
BRN 1357507 [DBID]
C00397 [DBID]
CHEBI:28864 [DBID]
D00063 [DBID]
HSDB 3259 [DBID]
KBio2_001552 [DBID]
KBio2_004120 [DBID]
KBio2_006688 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth Q-201838
      GHS07; GHS08 Biosynth Q-201838
      H302; H312; H332 Biosynth Q-201838
      J01GB01 Wikidata Q1758380
      P101; P201; P280; P281; P308+P313 Biosynth Q-201838
      S01AA12 Wikidata Q1758380
    • Target Organs:

      Antibacterial TargetMol T1255
    • Chemical Class:

      A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring. ChEBI CHEBI:28864
      aminoglycoside Microsource [01500579]
    • Drug Status:

      approved BIONET-Key Organics KS-1405
    • Compound Source:

      Streptomyces spp Microsource [01500579]
    • Bio Activity:

      30S ribosomal protein TargetMol T1255
      Aminoglycoside antibiotic Tocris Bioscience 5390
      Aminoglycoside antibiotic. Exhibits antibacterial activity against strains of Enterobacteriaceae, Pseudomonas and Staphylococcus aureus. Shown to protect lung epithelial cells in vitro against injury from cystic fibrosis bronchial secretions and H2O2. Tocris Bioscience 5390
      Aminoglycoside antibiotic. Exhibits antibacterial activity against strains of Enterobacteriaceae, Pseudomonas and Staphylococcus aureus. Shown to protect lung epithelial cells in vitro against injury from cystic fibrosis bronchial secretions and H2O2. Tocris Bioscience 5390
      Antibacterial MedChem Express HY-B0441
      Antibiotics Tocris Bioscience 5390
      Anti-infection MedChem Express HY-B0441
      Anti-infection; MedChem Express HY-B0441
      Microbiology & Virology TargetMol T1255
      Other Pharmacology Tocris Bioscience 5390
      Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. MedChem Express
      Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius.; Target: Antibacterial; Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius and used to treat various types of bacterial infections, particularly Gram-negative infections. MedChem Express HY-B0441
      Tobramycin is an aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius.;Target: Antibacterial;Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius and used to treat various types of bacterial infections, particularly Gram-negative infections. It is especially effective against species of Pseudomonas [1]. ;Tobramycin works by binding to a site on the bacterial 30S and 50S ribosome, preventing formation of the 70S complex. As a result, mRNA cannot be translated into protein and cell death ensues. Tobramycin is preferred over gentamicin for Pseudomonas aeruginosa pneumonia due to better lung penetration. From Wikipedia [2]. MedChem Express HY-B0441

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.5±0.1 g/cm3
Boiling Point: 775.4±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±6.0 mmHg at 25°C
Enthalpy of Vaporization: 128.7±6.0 kJ/mol
Flash Point: 422.8±32.9 °C
Index of Refraction: 1.651
Molar Refractivity: 111.7±0.4 cm3
#H bond acceptors: 14
#H bond donors: 15
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 2
ACD/LogP: -3.41
ACD/LogD (pH 5.5): -10.91
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -9.45
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 268 Å2
Polarizability: 44.3±0.5 10-24cm3
Surface Tension: 92.7±5.0 dyne/cm
Molar Volume: 305.9±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -5.76

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  699.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  305.74  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.37E-021  (Modified Grain method)
    Subcooled liquid VP: 3.29E-018 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1e+006
       log Kow used: -5.76 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.24E-039  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.458E-027 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -5.76  (KowWin est)
  Log Kaw used:  -37.038  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  31.278
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6983
   Biowin2 (Non-Linear Model)     :   0.0020
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0534  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9979  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6118
   Biowin6 (MITI Non-Linear Model):   0.0003
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.7216
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  4.39E-016 Pa (3.29E-018 mm Hg)
  Log Koa (Koawin est  ): 31.278
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.84E+009 
       Octanol/air (Koa) model:  4.66E+018 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 362.5860 E-12 cm3/molecule-sec
      Half-Life =     0.029 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    21.239 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -5.76 (estimated)

 Volatilization from Water:
    Henry LC:  2.24E-039 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.652E+035  hours   (2.355E+034 days)
    Half-Life from Model Lake : 6.165E+036  hours   (2.569E+035 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       3.35e-020       0.708        1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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